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MDW - SFB

$102 Find cheap flights from Chicago Midway Airport to Orlando Sanford Intl

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Orlando departing on 6/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/15
Sat 6/22

Search hundreds of travel sites at once for deals on flights to Orlando Sanford Intl

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Orlando, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Orlando, as well as popular online travel agencies
In the last 7 days travelers have searched 42,211,976 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Midway to Orlando (MDW-SFB)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Orlando that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:30 pm - 4:20 pmMDW-SFB
18h 50m1 stop
9:44 pm - 7:40 pmSFB-MDW
22h 56m1 stop
$229Allegiant Air
Find Deal
Fri, Aug 2 - Sun, Aug 4
2:14 pm - 7:58 amMDW-SFB
16h 44m1 stop
8:54 am - 7:44 pmSFB-MDW
11h 50m1 stop
$233Allegiant Air
Find Deal
Fri, Jun 7 - Mon, Jun 10
2:14 pm - 7:58 amMDW-SFB
16h 44m1 stop
8:54 am - 8:18 pmSFB-MDW
12h 24m1 stop
$236Allegiant Air
Find Deal
Fri, Jun 14 - Mon, Jun 17
8:33 pm - 10:36 amMDW-SFB
13h 03m1 stop
9:33 pm - 1:24 pmSFB-MDW
16h 51m1 stop
$239Allegiant Air
Find Deal
Fri, May 31 - Sun, Jun 9
8:33 pm - 10:36 amMDW-SFB
13h 03m1 stop
8:56 am - 7:43 pmSFB-MDW
11h 47m1 stop
$240Allegiant Air
Find Deal
Fri, May 31 - Mon, Jun 3
9:08 pm - 10:04 amMDW-SFB
11h 56m1 stop
9:18 am - 8:17 pmSFB-MDW
11h 59m1 stop
$247Allegiant Air
Find Deal
Mon, Jul 1 - Fri, Jul 5
3:12 pm - 10:06 amMDW-SFB
17h 54m1 stop
8:56 am - 7:43 pmSFB-MDW
11h 47m1 stop
$279Allegiant Air
Find Deal
Mon, May 27 - Fri, May 31
9:08 pm - 12:34 pmMDW-SFB
14h 26m1 stop
8:54 am - 8:18 pmSFB-MDW
12h 24m1 stop
$281Allegiant Air
Find Deal
Fri, Jun 14 - Fri, Jun 21
9:08 pm - 12:34 pmMDW-SFB
14h 26m1 stop
8:54 am - 8:18 pmSFB-MDW
12h 24m1 stop
$282Allegiant Air
Find Deal
Fri, Jun 14 - Fri, Jun 21
9:07 pm - 10:03 amMDW-SFB
11h 56m1 stop
9:18 am - 7:40 pmSFB-MDW
11h 22m1 stop
$289Allegiant Air
Find Deal
Mon, Jul 22 - Mon, Jul 29

Flights from Midway to Orlando - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Orlando to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago Midway Airport to Orlando Sanford Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Orlando Sanford Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Orlando Sanford Intl Airport is September, where tickets cost $88 on average. On the other hand, the most expensive months are February and December, where the average cost of tickets is $339 and $294 respectively.

Good to know

Cheapest flight

$102
Flight from Chicago Midway Airport to Orlando Sanford Intl

When to book flights from Midway to Orlando

Are your dates flexible? Find out the best times to travel from Midway to Orlando based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Orlando Sanford Intl flights

  • What is the cheapest flight from Chicago Midway Airport to Orlando Sanford Intl Airport?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Orlando Sanford Intl Airport was $102 for a one-way ticket and $229 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Orlando Sanford Intl?

    No

  • Which aircraft models fly most regularly from Chicago Midway Airport to Orlando Sanford Intl?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Orlando Sanford Intl?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Orlando Sanford Intl.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Orlando Sanford Intl?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Orlando Sanford Intl from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Orlando Sanford Intl?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Orlando Sanford Intl with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SFB can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Orlando Sanford Intl?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Orlando Sanford Intl from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Midway to Orlando

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Orlando. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Orlando? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
6.2
FrontierOverall score based on 4060 reviews
7.1Crew
5.8Comfort
5.2Food
4.9Entertainment
6.6Boarding
Airline reviews

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

2.0 Mediocrejohn, Apr 2024IAH - MCO
Read more about Frontier reviews

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight delayed 3 times, resulting in late arrival, rental car place gave car away resulting in increased BS charges because I was late. Frontier blows.

It was impossible to change a carry-on for a checked bag after the initial selection. The flight was delayed 14 hours "to allow for a late arriving aircraft." The seats were shockingly uncomfortable. This was only the second time I've seen seats that didn't recline in an airline. The first was in an East Bloc airline before the fall if the Iron Curtain.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Everything was on time and smoothly run. All employees appeared happy and enjoying their job. The delay in take-off was unrelated to anything in Frontier’s control. I wish there were a caffeine-fee, sugar free soda drink option besides water. There are multiple zero sugar caffeine free options.

Everything was on time and smoothly run. All employees appeared happy and enjoying their job. The delay in take-off was unrelated to anything in Frontier’s control.

I like that the flight was not overcrowded, and I felt had space to spread out a little more. The flight was smooth for the most part no major turbulence. The crew was pretty good accommodating and professional.. the fellow passengers were cool as well… all good! Snacks always makes things better, but of course there were no snacks.

Be prepared for crowds and chaos upon arrival at the Orlando airport

Frontier is a mess. Kept changing flights and times on me. Ridiculous. Charged us twice for annual Discout Den membership.

Book cheap flights from Chicago to Orlando

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Orlando found on KAYAK in the last 72 hours.
6/10Mon
1 stopAllegiant Air
12h 30mMDW-SFB
$102
6/17Mon
1 stopAllegiant Air
11h 56mMDW-SFB
$108
6/14Fri
1 stopAllegiant Air
14h 26mMDW-SFB
$124
5/31Fri
1 stopAllegiant Air
13h 03mMDW-SFB
$126
5/31Fri
1 stopAllegiant Air
13h 03mMDW-SFB
$129
5/27Mon
1 stopAllegiant Air
17h 54mMDW-SFB
$135
6/16Sun
2 stopsAllegiant Air
27h 00mMDW-SFB
$156
5/24Fri
1 stopAllegiant Air
28h 25mMDW-SFB
$195
5/24Fri
1 stopAllegiant Air
18h 24mMDW-SFB
$215
6/13Thu
2 stopsAllegiant Air
12h 32mMDW-SFB
$252

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Last minute flights from Midway to Orlando

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Orlando that are departing in the next 10 days.
5/17Fri
multi-stopAllegiant Air
28h 17mMDW-SFB
5/19Sun
multi-stopAllegiant Air
18h 29mSFB-MDW
$549
5/20Mon
multi-stopAllegiant Air
4h 43mMDW-SFB
5/26Sun
multi-stopAllegiant Air
16h 59mSFB-MDW
$580
5/20Mon
multi-stopAllegiant Air
4h 43mMDW-SFB
5/27Mon
multi-stopAllegiant Air
6h 56mSFB-MDW
$596
5/17Fri
multi-stopAllegiant Air
4h 43mMDW-SFB
5/25Sat
multi-stopAllegiant Air
24h 40mSFB-MDW
$615
5/19Sun
multi-stopAllegiant Air
25h 21mMDW-SFB
5/25Sat
multi-stopAllegiant Air
24h 40mSFB-MDW
$742
5/20Mon
multi-stopAllegiant Air
4h 43mMDW-SFB
5/26Sun
multi-stopAllegiant Air
27h 56mSFB-MDW
$794

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Chicago Midway Airport - Orlando Sanford Intl Flights

Departure:

Chicago Midway Airport (undefined)United States

Destination:

Orlando Sanford Intl (SFB)United States

Cabin classes:

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